NPASS Compound

Structure

NPC476065 OpenBabel07101719512D 35 38 0 0 1 0 0 0 0 0999 V2000 -4.7099 -5.1837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1847 -4.6650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8668 -1.6483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6505 -2.8646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2776 3.7632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8417 2.9193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9267 2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7438 -5.3108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9666 -0.3011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7648 1.2317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7705 -1.7626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5727 -0.7883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1507 -4.5378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9666 -1.2755 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2776 -1.9644 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2776 0.3879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6143 -1.2755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2776 2.0755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9267 -1.2755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3033 0.3879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6143 -0.3011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8161 1.2317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3033 -1.9644 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3033 2.0755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9267 -0.3011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7705 0.1861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5236 -3.6376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8417 1.2317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4896 -3.5105 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7648 2.9193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8161 2.9193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7705 2.1348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.5765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9304 -2.8646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 13 1 0 0 0 0 5 30 1 0 0 0 0 6 31 1 0 0 0 0 7 32 1 0 0 0 0 8 13 2 0 0 0 0 9 14 1 0 0 0 0 9 16 1 0 0 0 0 10 16 2 0 0 0 0 10 18 1 0 0 0 0 11 17 2 0 0 0 0 11 19 1 0 0 0 0 12 33 1 0 0 0 0 12 34 1 0 0 0 0 13 27 1 0 0 0 0 14 3 1 6 0 0 0 14 15 1 0 0 0 0 15 4 1 6 0 0 0 15 23 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 18 24 2 0 0 0 0 18 30 1 0 0 0 0 19 25 2 0 0 0 0 19 33 1 0 0 0 0 20 21 1 0 0 0 0 20 22 2 0 0 0 0 21 26 2 0 0 0 0 22 24 1 0 0 0 0 22 28 1 0 0 0 0 23 35 1 6 0 0 0 24 31 1 0 0 0 0 25 26 1 0 0 0 0 25 34 1 0 0 0 0 26 32 1 0 0 0 0 27 29 2 0 0 0 0 27 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.21
Volume:	490.552
LogP:	4.684
LogD:	4.407
LogS:	-5.049
# Rotatable Bonds:	6
TPSA:	92.68
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.458
Synthetic Accessibility Score:	4.125
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.768
MDCK Permeability:	2.2329297280521132e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	89.47832489013672%
Volume Distribution (VD):	0.696
Pgp-substrate:	10.348919868469238%

ADMET: Metabolism

CYP1A2-inhibitor:	0.121
CYP1A2-substrate:	0.972
CYP2C19-inhibitor:	0.972
CYP2C19-substrate:	0.894
CYP2C9-inhibitor:	0.947
CYP2C9-substrate:	0.883
CYP2D6-inhibitor:	0.509
CYP2D6-substrate:	0.685
CYP3A4-inhibitor:	0.856
CYP3A4-substrate:	0.902

ADMET: Excretion

Clearance (CL):	5.22
Half-life (T1/2):	0.189

ADMET: Toxicity

hERG Blockers:	0.085
Human Hepatotoxicity (H-HT):	0.135
Drug-inuced Liver Injury (DILI):	0.833
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.103
Skin Sensitization:	0.133
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.232
Respiratory Toxicity:	0.291

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC476065

Natural Product ID:	NPC476065
*Common Name:**	Angeloylbinankadsurin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CQWHTXPRAFEPNO-AWVVPDOTSA-N
Standard InCHI:	InChI=1S/C27H32O8/c1-8-13(2)27(29)35-23-15(4)14(3)9-16-10-18(30-5)24(31-6)22(28)20(16)21-17(23)11-19-25(26(21)32-7)34-12-33-19/h8,10-11,14-15,23,28H,9,12H2,1-7H3/b13-8-/t14-,15-,23-/m1/s1
SMILES:	CC=C(C)C(=O)OC1C(C(CC2=CC(=C(C(=C2C3=C(C4=C(C=C13)OCO4)OC)O)OC)OC)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL524283
PubChem CID:	12004413
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[16018647]
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[16018647]
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[16268562]
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16792420]
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17608535]
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	3
Others	1

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	ED50	>=	5.0	ug ml-1	PMID[531549]
NPT91	Cell Line	KB	Homo sapiens	ED50	>=	5.0	ug ml-1	PMID[531549]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>=	5.0	ug ml-1	PMID[531549]
NPT1	Others	Radical scavenging activity		Activity	=	2.3	%	PMID[531549]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC476065 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	335
0.1-0.2	1442
0.2-0.3	3597
0.3-0.4	8577
0.4-0.5	9949
0.5-0.6	3813
0.6-0.7	6580
0.7-0.8	7036
0.8-0.85	1088
0.85-0.9	198
0.9-0.95	58
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
0.9866	High Similarity	NPC475592
0.9796	High Similarity	NPC471154
0.973	High Similarity	NPC53669
0.973	High Similarity	NPC297271
0.973	High Similarity	NPC217708
0.973	High Similarity	NPC308739
0.973	High Similarity	NPC24562
0.973	High Similarity	NPC474606
0.973	High Similarity	NPC126405
0.973	High Similarity	NPC16791
0.973	High Similarity	NPC77237
0.9728	High Similarity	NPC475756
0.9669	High Similarity	NPC215400
0.9669	High Similarity	NPC230531
0.96	High Similarity	NPC238834
0.9595	High Similarity	NPC224472
0.9592	High Similarity	NPC474393
0.9592	High Similarity	NPC474347
0.9536	High Similarity	NPC473323
0.9533	High Similarity	NPC312763
0.9533	High Similarity	NPC198461
0.9527	High Similarity	NPC470916
0.9524	High Similarity	NPC477375
0.9524	High Similarity	NPC327352
0.9524	High Similarity	NPC252281
0.9524	High Similarity	NPC198129
0.9459	High Similarity	NPC477376
0.9459	High Similarity	NPC477374
0.9459	High Similarity	NPC322426
0.9396	High Similarity	NPC316989
0.9392	High Similarity	NPC325720
0.9392	High Similarity	NPC316676
0.9338	High Similarity	NPC149735
0.9329	High Similarity	NPC85141
0.9324	High Similarity	NPC295297
0.932	High Similarity	NPC318286
0.932	High Similarity	NPC327651
0.9276	High Similarity	NPC473425
0.9267	High Similarity	NPC473989
0.9257	High Similarity	NPC321958
0.9257	High Similarity	NPC321696
0.9257	High Similarity	NPC474054
0.9252	High Similarity	NPC121661
0.9252	High Similarity	NPC87883
0.9252	High Similarity	NPC73467
0.9252	High Similarity	NPC326144
0.9241	High Similarity	NPC311912
0.9211	High Similarity	NPC477377
0.9211	High Similarity	NPC475141
0.9189	High Similarity	NPC110763
0.9189	High Similarity	NPC189239
0.9189	High Similarity	NPC197352
0.9189	High Similarity	NPC166506
0.9184	High Similarity	NPC218510
0.9184	High Similarity	NPC76415
0.9182	High Similarity	NPC88557
0.9156	High Similarity	NPC29727
0.915	High Similarity	NPC473736
0.9145	High Similarity	NPC475229
0.9145	High Similarity	NPC477378
0.9139	High Similarity	NPC24425
0.9139	High Similarity	NPC477381
0.9128	High Similarity	NPC252286
0.9128	High Similarity	NPC154971
0.9116	High Similarity	NPC184684
0.9116	High Similarity	NPC133934
0.9116	High Similarity	NPC184641
0.9079	High Similarity	NPC477379
0.906	High Similarity	NPC477702
0.9057	High Similarity	NPC83049
0.9057	High Similarity	NPC118162
0.9057	High Similarity	NPC320471
0.9054	High Similarity	NPC324962
0.9051	High Similarity	NPC469475
0.9051	High Similarity	NPC469518
0.9032	High Similarity	NPC477380
0.9026	High Similarity	NPC348849
0.9026	High Similarity	NPC178195
0.9	High Similarity	NPC212890
0.8987	High Similarity	NPC469512
0.8986	High Similarity	NPC230538
0.8986	High Similarity	NPC229172
0.8986	High Similarity	NPC103637
0.8986	High Similarity	NPC36531
0.8974	High Similarity	NPC477885
0.894	High Similarity	NPC183083
0.894	High Similarity	NPC137352
0.8933	High Similarity	NPC475868
0.8912	High Similarity	NPC471183
0.8882	High Similarity	NPC477879
0.8882	High Similarity	NPC252402
0.8882	High Similarity	NPC79322
0.8882	High Similarity	NPC102934
0.8868	High Similarity	NPC42797
0.8868	High Similarity	NPC473445
0.8867	High Similarity	NPC172171
0.8867	High Similarity	NPC239254
0.8861	High Similarity	NPC63061
0.8844	High Similarity	NPC865
0.8834	High Similarity	NPC471181
0.8834	High Similarity	NPC178737
0.8831	High Similarity	NPC303519
0.8831	High Similarity	NPC477700
0.8831	High Similarity	NPC32079
0.8812	High Similarity	NPC291977
0.8805	High Similarity	NPC319749
0.8797	High Similarity	NPC325122
0.8784	High Similarity	NPC290714
0.8784	High Similarity	NPC201404
0.8784	High Similarity	NPC53722
0.8776	High Similarity	NPC133025
0.8773	High Similarity	NPC477883
0.8758	High Similarity	NPC304821
0.8742	High Similarity	NPC268718
0.8742	High Similarity	NPC297342
0.8742	High Similarity	NPC118385
0.8742	High Similarity	NPC91634
0.8742	High Similarity	NPC472713
0.8742	High Similarity	NPC150943
0.8742	High Similarity	NPC472712
0.8742	High Similarity	NPC187774
0.8742	High Similarity	NPC473046
0.8734	High Similarity	NPC115281
0.8734	High Similarity	NPC163527
0.8734	High Similarity	NPC181168
0.8733	High Similarity	NPC287124
0.8733	High Similarity	NPC41782
0.8725	High Similarity	NPC177868
0.872	High Similarity	NPC469506
0.8716	High Similarity	NPC86605
0.8716	High Similarity	NPC3072
0.8716	High Similarity	NPC46277
0.8716	High Similarity	NPC474039
0.8716	High Similarity	NPC301765
0.8716	High Similarity	NPC156948
0.8701	High Similarity	NPC90896
0.8701	High Similarity	NPC283839
0.8701	High Similarity	NPC474965
0.8701	High Similarity	NPC106138
0.8701	High Similarity	NPC293757
0.8701	High Similarity	NPC174512
0.8701	High Similarity	NPC668
0.8701	High Similarity	NPC477695
0.8696	High Similarity	NPC475865
0.8688	High Similarity	NPC258322
0.8688	High Similarity	NPC191352
0.8679	High Similarity	NPC241600
0.8679	High Similarity	NPC173726
0.8675	High Similarity	NPC469630
0.8675	High Similarity	NPC12728
0.8675	High Similarity	NPC185071
0.8671	High Similarity	NPC469474
0.8671	High Similarity	NPC228357
0.8667	High Similarity	NPC477881
0.8662	High Similarity	NPC136757
0.8658	High Similarity	NPC6369
0.8658	High Similarity	NPC30951
0.8654	High Similarity	NPC302610
0.8654	High Similarity	NPC478268
0.8654	High Similarity	NPC477699
0.8654	High Similarity	NPC476434
0.865	High Similarity	NPC471180
0.8649	High Similarity	NPC143895
0.8645	High Similarity	NPC472709
0.8645	High Similarity	NPC472710
0.8645	High Similarity	NPC469707
0.8645	High Similarity	NPC214326
0.8645	High Similarity	NPC260781
0.8645	High Similarity	NPC145979
0.8645	High Similarity	NPC182368
0.8645	High Similarity	NPC218041
0.8645	High Similarity	NPC469706
0.8645	High Similarity	NPC225815
0.8645	High Similarity	NPC9933
0.8645	High Similarity	NPC185955
0.8642	High Similarity	NPC477884
0.8639	High Similarity	NPC289258
0.8639	High Similarity	NPC56764
0.8639	High Similarity	NPC276026
0.8639	High Similarity	NPC469659
0.8639	High Similarity	NPC555
0.8639	High Similarity	NPC206737
0.8639	High Similarity	NPC256776
0.8639	High Similarity	NPC188378
0.8639	High Similarity	NPC7515
0.8639	High Similarity	NPC185680
0.8639	High Similarity	NPC145722
0.8634	High Similarity	NPC280778
0.8625	High Similarity	NPC474770
0.8618	High Similarity	NPC477701
0.8618	High Similarity	NPC166884
0.8618	High Similarity	NPC141569
0.8616	High Similarity	NPC125495
0.8616	High Similarity	NPC207584
0.8616	High Similarity	NPC19947
0.8609	High Similarity	NPC472714
0.8609	High Similarity	NPC191231
0.8609	High Similarity	NPC67467
0.8609	High Similarity	NPC5262
0.8608	High Similarity	NPC117154

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC476065 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	290
0.1-0.2	895
0.2-0.3	1830
0.3-0.4	2753
0.4-0.5	1760
0.5-0.6	960
0.6-0.7	548
0.7-0.8	105
0.8-0.85	5
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8797	High Similarity	NPD6234	Discontinued
0.8599	High Similarity	NPD37	Approved
0.8553	High Similarity	NPD4965	Approved
0.8553	High Similarity	NPD4966	Approved
0.8553	High Similarity	NPD4967	Phase 2
0.8537	High Similarity	NPD7228	Approved
0.8232	Intermediate Similarity	NPD7199	Phase 2
0.8228	Intermediate Similarity	NPD1653	Approved
0.8133	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD3818	Discontinued
0.8054	Intermediate Similarity	NPD3027	Phase 3
0.8052	Intermediate Similarity	NPD7266	Discontinued
0.8012	Intermediate Similarity	NPD7240	Approved
0.7988	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7074	Phase 3
0.7866	Intermediate Similarity	NPD1465	Phase 2
0.7836	Intermediate Similarity	NPD7054	Approved
0.7826	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7473	Discontinued
0.7791	Intermediate Similarity	NPD7472	Approved
0.7778	Intermediate Similarity	NPD1613	Approved
0.7778	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD3705	Approved
0.7751	Intermediate Similarity	NPD6232	Discontinued
0.775	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD5844	Phase 1
0.7701	Intermediate Similarity	NPD6559	Discontinued
0.7697	Intermediate Similarity	NPD1934	Approved
0.7682	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD3882	Suspended
0.7657	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6674	Discontinued
0.76	Intermediate Similarity	NPD7685	Pre-registration
0.76	Intermediate Similarity	NPD7251	Discontinued
0.7598	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7808	Phase 3
0.7548	Intermediate Similarity	NPD4060	Phase 1
0.7545	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD6797	Phase 2
0.7515	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3817	Phase 2
0.7487	Intermediate Similarity	NPD7680	Approved
0.7457	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD6166	Phase 2
0.7457	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7819	Suspended
0.744	Intermediate Similarity	NPD2801	Approved
0.7438	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7075	Discontinued
0.7389	Intermediate Similarity	NPD230	Phase 1
0.7378	Intermediate Similarity	NPD2534	Approved
0.7378	Intermediate Similarity	NPD2532	Approved
0.7378	Intermediate Similarity	NPD2533	Approved
0.7348	Intermediate Similarity	NPD6843	Phase 3
0.7348	Intermediate Similarity	NPD6841	Approved
0.7348	Intermediate Similarity	NPD6842	Approved
0.7346	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD3750	Approved
0.7326	Intermediate Similarity	NPD5494	Approved
0.7308	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6190	Approved
0.729	Intermediate Similarity	NPD4908	Phase 1
0.7283	Intermediate Similarity	NPD8127	Discontinued
0.7278	Intermediate Similarity	NPD6355	Discontinued
0.7267	Intermediate Similarity	NPD5762	Approved
0.7267	Intermediate Similarity	NPD5763	Approved
0.7262	Intermediate Similarity	NPD4380	Phase 2
0.7241	Intermediate Similarity	NPD7229	Phase 3
0.7235	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD8455	Phase 2
0.7232	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3018	Phase 2
0.7222	Intermediate Similarity	NPD8313	Approved
0.7222	Intermediate Similarity	NPD8312	Approved
0.7215	Intermediate Similarity	NPD3620	Phase 2
0.7215	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1511	Approved
0.7209	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD3751	Discontinued
0.7171	Intermediate Similarity	NPD1610	Phase 2
0.7171	Intermediate Similarity	NPD422	Phase 1
0.7167	Intermediate Similarity	NPD7549	Discontinued
0.7151	Intermediate Similarity	NPD7768	Phase 2
0.7134	Intermediate Similarity	NPD4625	Phase 3
0.7134	Intermediate Similarity	NPD4628	Phase 3
0.7126	Intermediate Similarity	NPD1512	Approved
0.7126	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2861	Phase 2
0.7113	Intermediate Similarity	NPD8151	Discontinued
0.7108	Intermediate Similarity	NPD4357	Discontinued
0.7108	Intermediate Similarity	NPD6799	Approved
0.7099	Intermediate Similarity	NPD2935	Discontinued
0.7093	Intermediate Similarity	NPD5402	Approved
0.7086	Intermediate Similarity	NPD1357	Approved
0.7086	Intermediate Similarity	NPD6959	Discontinued
0.7078	Intermediate Similarity	NPD2982	Phase 2
0.7078	Intermediate Similarity	NPD2983	Phase 2
0.7076	Intermediate Similarity	NPD6801	Discontinued
0.7073	Intermediate Similarity	NPD1652	Phase 2
0.7069	Intermediate Similarity	NPD919	Approved
0.7063	Intermediate Similarity	NPD5124	Phase 1
0.7063	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1091	Approved
0.7059	Intermediate Similarity	NPD6599	Discontinued
0.7051	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3787	Discontinued
0.7039	Intermediate Similarity	NPD4626	Approved
0.7037	Intermediate Similarity	NPD3748	Approved
0.703	Intermediate Similarity	NPD4110	Phase 3
0.703	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD8166	Discontinued
0.7027	Intermediate Similarity	NPD5283	Phase 1
0.7013	Intermediate Similarity	NPD2981	Phase 2
0.7011	Intermediate Similarity	NPD3749	Approved
0.7011	Intermediate Similarity	NPD8434	Phase 2
0.7006	Intermediate Similarity	NPD3926	Phase 2
0.7	Intermediate Similarity	NPD7458	Discontinued
0.6994	Remote Similarity	NPD2438	Suspended
0.6994	Remote Similarity	NPD5353	Approved
0.6994	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6100	Approved
0.6994	Remote Similarity	NPD6099	Approved
0.6982	Remote Similarity	NPD5403	Approved
0.6981	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7097	Phase 1
0.6974	Remote Similarity	NPD5691	Approved
0.6968	Remote Similarity	NPD4749	Approved
0.6964	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7028	Phase 2
0.6954	Remote Similarity	NPD5536	Phase 2
0.6936	Remote Similarity	NPD2977	Approved
0.6936	Remote Similarity	NPD2978	Approved
0.6936	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1510	Phase 2
0.6919	Remote Similarity	NPD7411	Suspended
0.6919	Remote Similarity	NPD7827	Phase 1
0.6919	Remote Similarity	NPD5090	Approved
0.6919	Remote Similarity	NPD5089	Approved
0.6919	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7095	Approved
0.6914	Remote Similarity	NPD6653	Approved
0.691	Remote Similarity	NPD5242	Approved
0.6909	Remote Similarity	NPD1549	Phase 2
0.6908	Remote Similarity	NPD1548	Phase 1
0.6901	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1240	Approved
0.6892	Remote Similarity	NPD228	Approved
0.6891	Remote Similarity	NPD5006	Approved
0.6891	Remote Similarity	NPD5005	Approved
0.689	Remote Similarity	NPD1551	Phase 2
0.6879	Remote Similarity	NPD2797	Approved
0.6875	Remote Similarity	NPD6798	Discontinued
0.6875	Remote Similarity	NPD3764	Approved
0.6872	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5401	Approved
0.6864	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD7296	Approved
0.6859	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD7435	Discontinued
0.6854	Remote Similarity	NPD5710	Approved
0.6854	Remote Similarity	NPD5711	Approved
0.6852	Remote Similarity	NPD447	Suspended
0.6852	Remote Similarity	NPD1933	Approved
0.6848	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1283	Approved
0.681	Remote Similarity	NPD1607	Approved
0.6802	Remote Similarity	NPD4005	Discontinued
0.6798	Remote Similarity	NPD1247	Approved
0.679	Remote Similarity	NPD4140	Approved
0.679	Remote Similarity	NPD2979	Phase 3
0.679	Remote Similarity	NPD943	Approved
0.6788	Remote Similarity	NPD2796	Approved
0.6786	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3496	Discontinued
0.6771	Remote Similarity	NPD4420	Approved
0.677	Remote Similarity	NPD3268	Approved
0.6766	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7930	Approved
0.6765	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3022	Approved
0.6757	Remote Similarity	NPD3021	Approved
0.6747	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD3540	Phase 1
0.6747	Remote Similarity	NPD6002	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data